


Benefits

by abeautifullie3



Category: Supernatural
Genre: Age Difference, F/M, Het, Pre-Series, Written for Charity
Language: English
Status: Completed
Published: 2014-03-26
Updated: 2014-03-26
Packaged: 2018-01-17 02:22:18
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 7,023
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1370380
Author URL: https://archiveofourown.org/users/abeautifullie3/pseuds/abeautifullie3
Summary: <blockquote class="userstuff">
              <p>With John gone, Dean's having trouble making the rent.  An unexpected job offer makes things go smoothly for once, and ends up coming with some sweet benefits.</p>
            </blockquote>





	Benefits

**Author's Note:**

> **Warnings** : Barely legal Dean having relations with a "mature" woman - I suppose this could squick some people. Mentions of bad-father John. Pre-series, so no spoilers.  
>  **Disclaimer** : The story and Olivia the landlady, are mine. The boys, and all things canon, not mine. *pouts*
> 
>  **Originally Posted Here** ::: http://abeautifullie3.livejournal.com/33219.html

 

 

 

x~X~x  **Benefits**   x~X~x

 

    "Dad call yet?" Sam looked up from his science book, his face etched in worry as he glanced warily at his big brother.

    Dean dropped the bags of groceries on the counter with a thud, and angrily threw open the refrigerator door. "No."

    "Rent's already past due and..."

    "Don't you think I know that, Sam? I'm doin' the best I can here." Dean shoved the milk into the fridge and slammed the door, storming over to throw the rest of the groceries into the cupboards.

    "I know you are, Dean. I'm sorry, didn't mean to...I could try to get a job? After school? I got the ID that says I'm..."

    "No," Dean interrupted Sam, dropping a heavy hand on his shoulder, then giving it at reassuring squeeze. "You focus on school; I'll take care of it. Gonna take a shower, then I'll fix dinner."

    Sam nodded on a deep sigh, and watched Dean shuffle down the hall, before going back to his homework.

 

    Shucking off his clothes, and climbing under the hot spray of the shower, Dean vigorously scrubbed off a 12-hr shift worth of diner grease. The job sucked, but they paid him under the table, let him eat for free, and he was usually home for Sam in the evenings. Still, they only needed him a few days a week, and it simply wasn't enough. So far, he hadn't had any luck finding something to fill the other days - and thus make enough cash to cover things until his Dad showed up again.  
    Dean was pissed at his Dad this time. John had promised Dean it would only be a week tops; better for the boys to stay put - not yank Sam out of school for this one. Dean had known better, tried to tell his father otherwise, but John - as always - refused to listen. That was three weeks ago, and Dean hadn't even heard from him in the last eight days of it. To top it off, just like usual, the money he'd left had run out two weeks ago. It was almost like John couldn't leave more than enough cash for how long he _claimed_ he'd be gone, like it would be admitting he knew his time frames were always bullshit. For as much as Dean loved his father, sometimes he couldn't help but think he and Sam would be better off on their own.  
    Leaning his head against the wall, Dean tried to relax and let the still hot water sooth away some of his tension. At least that was something to be thankful for. Most places they'd stayed at this cheap, were total dives. No hot water, broken furniture, druggies and working-girls for neighbors, and things that scurried in the dark corners that you _wished_ were rather a demon or shifter. This place wasn't The Ritz, but it was decent. Things worked, the place was clean, and they could sleep peacefully without worry of vermin - neighbors or otherwise. Dean desperately wanted to keep a hold of the place, but so far he only had half the rent. Yeah, he was so screwed.

    "Dean!" Sam burst into the bathroom. "Someone's at the door."

    "Shit," Dean hissed. Grabbing a towel he stepped out of the shower. "Don't open it, just tell 'em to hold on a minute."

    "OK." Sam dashed out to the living room.

    Dean could hear him telling the person to wait, as he quickly slipped on a pair of sweats and his last clean t-shirt. Great, one more thing to worry about. Dean jogged down the hall to the front door. "I'm comin'. Who is it?" he asked, hand hesitating over the deadbolt.

    "Ms. Fletcher. Your landlady," a confident, but pleasant voice answered from the other side of the door.

    " _Landlady?_ " Sam mouthed.

    Dean shrugged as he turned the lock. They'd been there for about 4 months, but his Dad had taken care of the rent and there had been no other reason for the landlord - err, lady - to be mentioned. "Hey. Hi." Dean ran his hand through his spiky, wet hair - partly from nerves, partly from a need to distract himself from allowing his eyes to land on the great set of tits that greeted him on opening the door.

    Olivia Fletcher rocked back on her heels, hands tucked into the back pockets of her faded blue jeans, and smirk on lock down the second she noticed the kid trying not to stare at her rack. "Hey, kid. Your dad home?"

    "He's outta town, on business," Sam piped up.

    "Sammy!" Dean shot his brother a warning glare. "Why don't you go get cleaned up for dinner."

    Sam grumbled, but traipsed down the hall to the bathroom at his brother's demand.

    "Yeah, umm, like my brother said, he's out of town. Should be back any day now, just took him a little longer than planned." Dean nervously licked his lips and rubbed at the back of his neck. "Look, I know why you're here, and I got most of it, just...if you could..."

    "Give you a few extra days?" Olivia supplied. She watched as the kid nodded shyly. She was kinda fascinated by him. He had the cutest damn nervous gestures she had ever seen. Big, hazel-green eyes blinking rapidly; tongue flicking out repeatedly over sinfully plush lips; and the bashful way he ducked his head - hiding the pop of freckles against the blush on his face.

    Dean looked up hopefully, teeth sunk into his lower lip. "Could you? Three...four days tops? I promise I'll bring it right to ya."

    "That'd be fine. I'm on the top floor, end of the hall, 9C." Olivia took Dean's outstretched hand.

    "Thank you Ms. Fletcher. I really appreciate it, and I know my dad will too." Dean shook the woman's hand, totally not letting his gaze drift over the tanned cleavage busting out of the woman's way-too-many-buttons-unbuttoned gray henley.

    "You're welcome..."

    "Dean. I'm Dean."

    "Okay, well you take care of your brother there, Dean, and I'll see you in a few days." Olivia flashed Dean a big smile, gave him a quick wink, then walked down the hall - knowing full well the kid's eyes trailed her until she reached the stairs.

    Dean closed the door, leaning against it heavily. He momentarily entertained the idea of spending the evening on the couch, a little quality time with his hand along with visions of the hot as hell landlady dancing in his head after Sam went to bed. He knew that wouldn't be happening though. He was going to have to go out.

    "So? Are we gonna get kicked out?" Sam asked, coming back out and heading to the kitchen to help fix dinner.

    "Not if I can help it. She's giving us a few days, so after dinner I'm gonna have to go out. You keep the door locked - don't answer it for anyone - and don't answer the phone either, unless it's me or dad calling. Got it?"

    "Yeah, I got it." Sam rolled his eyes. "What are you going to do though?"

    "What I always do for fast cash: pool and poker."

    Sam stopped pulling out pans and turned to look at Dean. "But, Dad said no bars while he was gone, what if..."

    Dean walked to the fridge and started pulling out fixings for dinner. "It'll be fine, Sammy. I'll be careful. Besides, it's not like I really have a choice."

 

**x~X~x**

  
    There were a good handful of bars within walking distance of the apartment, which gave Dean a decent stalking ground. His first stop of the night was Mac's Tavern, where he was able to join in on a solid poker game. He managed to win a couple hundred, but let the guys win back about half. Dean hated to do it, but it kept anyone from getting pissed-off, and better left the way clear to playing again. He upped his winning another fifty at Mary's Tap, then headed down the block to The Fox's Den where the pool tables were really bustling. It took him awhile to get in on the action, but once he did, he was golden.

 

    Olivia saw the kid come in, knew of course he wasn't anywhere near old enough to be in the place, but she wasn't going to rat him out. Sitting in a both in the back corner, she didn't figure he would notice her there, yet she had a perfect view of him.  
    Straight off, Olivia found herself surprised by the kid's confidence - no real evidence of his earlier shyness. He didn't even show a hint of nervousness as he walked to the bar and ordered a beer, casually leaning against the bar and giving an easy nod as he flashed his ID and paid for his drink. She figured his ID must be a good one. No way it wasn't a fake, but she knew Bill the bartender had a keen eye for the decoys.  
    This was the first time she had seen him come in, and she was there nearly every night. Wondering what he was doing in some blue-collar bar, she watched him scan the place. Maybe casually observing, as she often did herself, or perhaps looking for a potential hook-up - though she figured him more for hitting a college bar for that. When she saw him join in on a couple games of pool, she chalked his reasons up to plain boredom, but as things progressed - while likely not evident to anyone not focused on his every move - it was clear to Olivia what he was doing. Sitting there alone, drinking her rum and coke, she was watching the kid make the rent money owed to her.  
    "Well shit," she cursed under her breath, to no one but herself. It wasn't like she had anything to feel guilty about, but she couldn't help it. She tried to shake it by telling herself this obviously wasn't his first time hustling pool. He'd done this before - probably a lot - yet knowing that this time, at least, was to keep a roof over him and his little brother, it shook loose to the surface some maternal instincts she didn't really think she had.  
    As more time, and more games flew by, Olivia found herself impressed. The kid was good, damn good. Not just at pool, but at keeping everything balanced. Letting other players win back just enough so they wouldn't catch on, yet staying well ahead on the winning end of things. Though she tried not to dwell on it - already feeling bad enough for something not her fault, she didn't need a legitimate reason for guilt - she was finding herself not only impressed by the kid, but turned on by him as well. Dean was gorgeous, that was obvious, but the way he moved: confident stride, body contouring to make difficult shots, hands deftly working the pool cue, and that perfect little ass on display every time he bent over the pool table. Olivia found her pulse racing as she wiggled in her seat, arousal already dampening her panties.  
    Olivia was flushing head to toe, and excited in a way that made her incredibly grateful to not be a dude. Filled with the sudden need to be home: slipping out of her tight jeans, under the bubbles of a tub full of hot water, and into an even hotter fantasy about the ways she'd like to get that kid moving for her, Olivia waited until Dean's back was turned to make her way out the rear entrance.

 

**x~X~x**

  
    "Dean! I'm _in_ here!" Sam stuck his soapy head out from behind the shower curtain, flashing his brother a look of pure, frustrated indignation.

    "Kid, I've diapered your ass, get the hell over it. I gotta take a leak, and not waitin' on you to play pretty princess in here all morning."

    "It's about respect." Sam huffed, and abrasively tugged the shower curtain closed.

    "Respect this..." Dean quickly finished - and flushed. "Freakin' teenagers."

    Sam screamed as the too-hot water hit him. "You _are_ a teenager, asshole!"

    Dean chose a non-verbal, one-fingered response to his brother, and left the bathroom to go forge for breakfast.

    By the time Sam came out, washed and dressed, back-pack flung on the sofa, Dean had eggs, bacon, and toast waiting. Most mornings it was cereal or pop-tarts, but he liked to fix a hot breakfast for the kid whenever he was up to it - and they had groceries. Sammy was growing like a weed, and it took a lot more than it used to keeping the cupboards full.

    Sam plopped down at the table, and dove into his food. "Thanks."

    "Welcome."

    "So how did you make out last night?"

    "Not too bad. Played it cool, figured I better keep the wells from dryin' up. Just in case."

    "Goin' back tonight?"

    "Yeah, and probably the next after work. Sorry, you're gonna be on your own for a few. You know the drill."

    Sam rolled his eyes and nodded. "Just...be careful."

    "I will."

    " 'cus if you get busted..."

    "I know, Sammy. Not gonna leave you on your own, alright?"

    Sam simply looked up at Dean through his shaggy bangs.

    "Promise. Now hurry up, you're gonna be late."

 

    Dean spent the day cleaning the small apartment, doing laundry, scanning the paper for another job, and even managed to squeeze in a little "personal" time in the shower while Sam was still at school. He'd been aching for a chance to take thoughts of their landlady for a spin through the pornier corners of his mind, and damn if she didn't look good taking the ride when he got her there. She was clearly old enough to be his mother, but Dean had been with more _mature_ women before, and they surely had their advantages. He'd learned some of his best moves that way. They were more nurturing, confident, and knew what they wanted; and hadn't hesitated providing Dean with instructions on how to give it.  
    Afternoon quickly passed to dinner time, and on to evening which led Dean to another night of poker and pool. Unbeknownst to him, it also placed him, once again, under the watchful and hungry gaze of Olivia, when he finished up hustling into the first morning hours at The Fox's Den. Dean called it a night well before closing, knowing that 6am and a 12-hr shift would be beckoning all too soon. Besides, he was close to having the money he needed, and didn't want to press his luck.

 

**x~X~x**

  
    Staring out the window of her apartment, Olivia caught sight of Dean coming down the block towards the building. The kid looked flat out shot to hell. She'd had a pisser of a day herself, the handyman she had for the small complex up and quitting on her with no notice. Struck with a sudden idea, Olivia didn't stop to think about it, instead throwing on her shoes - and stopping to take a quick look in the mirror - before grabbing her keys and rushing out the door.  
    Hurrying down the hall and stairs, Olivia could see Dean outside his door, exhausted and fumbling with his keys in the locks. "Hey, kid!"

    Dean dropped his keys on the floor. "Ms. Fletcher, hi. I uhh, was gonna' come by your place tomorrow. I thought..." Dean stammered as he bent over and grabbed his key-chain. "Look, I've got almost all of it. Maybe about fifty or sixty bucks short, but I swear I'll have..."

    "What do you know about leaky pipes, clogged drains, and spackling?" Olivia interrupted him.

    "Huh?" Dean looked at the woman like she'd sprouted another head. Which, he'd actually had prior experience with. It wasn't pleasant.

    "Are you any good with your hands?" Olivia paused, realizing though unintentional, how the question came out as she watched the kid blush and try not to smirk. "I meant...what I mean is...look, my handyman quit on me and I could use someone. Even if it's temporary."

    "I don't...I'm not a pro or anything, but I've picked-up a bit here and there. I just, I don't know how long we are going to be here."

    "Like I said, temp is fine, and the job comes with free rent plus pay."

    Dean wasn't getting any ominous vibes off the woman, if anything she seemed genuine and kind, maybe a little hint of... _no way, man, you're just horny and need to get laid_...but he'd never known anything that seemed too good to be true, not to be just that. "What's the catch?"

    A big smile spread over Olivia's face, as she stuck her hands in her back jean pockets and rocked back on her heels - her own nervous habit when she talked to people sometimes. "No catch, kid. I swear. You've got cash flow issues; I've got decent help issues. Just figured maybe we could help each other out. That's all. You can think about it, if you want. Let me know tomorrow. Or, spare yourself another late night hustling pool? Get a good night's sleep."

    Dean's eyes got huge. "I...you...how the hell?"

    "Relax, not following you or anything, and not gonna rat you out to anyone. Saw you at The Fox's Den a couple nights this week is all. Didn't say anything while I was there 'cus, well, didn't want to freak you out. Like I've managed to do anyway."

    " 'm not freaked, just." Dean rubbed at the back of his neck, licking his lips and sighing as he calmed himself. "I work three to four days a week at a diner, what kind of hours would you want me?"

    "Rather you be available twenty-four seven, for emergencies and such. Besides, with free rent and extra, would you really need to keep it?"

    "Guess not. And I could be around for Sammy more."

    "Good, it's settled. Come up to my apartment in the morning, and we'll sort the details then." Olivia gave Dean a wink and smile, then turned to hurry away before he could change his mind - not that she was certain he'd quite even truly had it made up.

    Dean grinned, partly confused about what had just happened, yet somewhat amused too. Running a hand through his sweaty hair, he turned to unlock the door when it was flung open briskly from the other side.

    "Free rent? Dude! And you hesitated?" Sam accosted his brother, as Dean just laughed at him, stepping into the apartment and locking the door behind them.

 

**x~X~x**

  
    The following morning, Dean went upstairs right after Sam left for school. He worried that it was too early, yet didn't want to keep Ms. Fletcher waiting on him either.  
    Finding her door, Dean gave a hesitant knock and waited, sighing with relief as the door promptly opened, and Ms. Fletcher smiled at him from behind her mug of - what smelled like - coffee. "I wasn't sure what time I should come up. Now a good time?"

    "Perfect. Want a cup of coffee?" Olivia stood back to let Dean in, then moved to the kitchen after closing the door behind him.

    "That'd be great."

    "Have a seat." Olivia tilted her head towards the small kitchen table. "Your brother get off to school alright?"

    "Yeah. Kid's a nerd. Likes all that school stuff, hates being late." Dean accepted a steaming mug from Ms. Fletcher, and tried to draw his eyes from the lose stands of hair falling across her face as she sat down. He'd only seen her with it pulled back, but with it lose, it made her look years younger. Drinking the strong, dark liquid, he tracked the strands as she casually tucked them behind her ear.

    "You look after him a lot, don't you? On your own I mean?" Olivia perched her elbows on the edge of the table, trying not to let on that she noticed Dean gazing at her - or her own more than casual observation in return.

    "I guess. Dad's got a hectic job. Do what I gotta do."

    "Are you eighteen, Dean?"

    Dean locked eyes with Olivia. And here was the catch. He didn't know what yet, but it was coming...he was sure.

    "As long as you're cool with it, I figure we'll keep this all off the books? I mean, we both know this isn't long term or anything. I just, well, with your dad gone, underage little brother and all, I'd feel a lot better knowing you're legal. Hell, lie to me even if you have to. Just make it convincing." Olivia winked.

    Or...no catch. "Eighteen, I swear. Turned a couple months back."

    "Good enough for me then." Olivia jumped up and grabbed a few things off the kitchen counter. "Here's a set of the master keys, and the pager I keep for the handyman. Basically, I get a repair call then I call you. There are keys to the basement: tools, equipment, cleaning supplies, also my washer and dryer are down there and you're free to use them. How you following so far?"

    "No problems."

    "If a repair seems too big I won't call you in, unless I think there might be a temp fix or clean-up needed. If you get there and the situation is out of your league, don't be afraid to tell me. I don't expect you to work miracles, just do what you can. Rents included in this, like I said, and how about we say three-hundred a week?"

    Dean blinked repeatedly, staring at the keys and pager. "I...Ms. Fletcher that's...thank you. I just hope I'm worth it."

    "I'm in a bind here, Dean. And I trust you can manage most of the things that go wrong around here, general maintenance, cleaning, the like. I think you'll be worth it." Olivia held out her hand to Dean, her breath hitching a little as he stood and gave it a firm shake. "And, Dean?"

    "Yeah?"

    "Call me Olivia."

    Dean smiled, nodded shyly, and reluctantly released her hand. "Olivia." Dean licked his lips.

    Olivia stepped back towards the fridge, and not forward like she wanted to. Her entire body was tingling with the desire to launch herself at the kid. Let her tongue trail over the plush lower lip his own tongue had just moistened; feel those strong, callus rough hands working over every heated inch of her body. Instead she did none of that, only doing what she should, and retrieving the 'To-Do' list off the fridge door. "Here's a list of some things to get you started. Don't worry about getting it all done right away, just ease yourself into it the first day or two. Any questions?"

    Dean shook his head. The only real question dancing behind his pursed lips, was an inappropriate one about just what exactly he'd like to be easing himself into at that moment.

    "Alright then, Dean, you think of any or have problems, my number's on the list." Olivia rather hurriedly walked Dean to the door, her restraint waning by the moment.

    "Thanks again, Olivia. I appreciate this. I won't let you down."

 

**x~X~x**

  
    The first week went well enough. The only real issue being Mrs. Lebowitz in 1B, who seemed to think Dean was her new BFF - or potentially a new family member. Every time he saw her, the old gal had another granddaughter, niece, or various unattached female relative she was certain he would be perfect for. Most of the time he didn't mind sparing a few minutes for her. She was lonely. Plus, she made awesome cookies. If he didn't think Sam would kill him in his sleep for it, he'd actually send the kid to go visit with her.  
    The second week was a little more challenging, the first problem he couldn't tackle arising, and he felt all kinds of lousy having to tell Olivia. She'd assured him it wasn't a big deal, but still he'd felt like he let her down. There were also two move-outs that week, and both needed cleaning, painting, and minor repairs. Dean ended up recruiting Sam to help with those, insisting he could pitch-in to help - but also giving him some pocket money when he'd done a good job with minimal bitching.  
    That was also the week Dad finally called. Although John didn't ask - he'd only called to check if Sam was alright, and tell Dean he'd be gone longer still - Dean told him about the arrangement. Dean had hoped for a "proud of you son", but only got, "That's fine, do a good job. Take care of your brother; I'll call when I can."

 

**x~X~x**

  
    The thunderstorm woke Dean. Small ones he'd sleep right through, but when they began to rage like this one was, he was up and pacing. He was just closing Sam's bedroom door - lucky kid could sleep through almost anything - when he heard the transformer blow, and watched the light from the bathroom flicker and fade.  
    "Shit." Dean made his way to the kitchen for the flashlight. It was the middle of the night, and most folks would be sleeping through the blackout. Being the handyman though, Dean felt the urge to check things out. Having heard the transformer, there likely was nothing he could do, but he was awake anyway. Leaving a quick note for Sam - should he unlikely wake-up and freak with Dean gone - Dean pulled on his jeans and shoes, and threw on a shirt not even bothering to button it up. Flashlight in hand, keys in his pocket, he locked up the apartment and headed for the power box in the basement.

 

    Dean heard the shriek the moment he turned the corner. His flashlight caught Olivia in its beam; her own flashlight hitting the floor and going black as she stood frozen in her short robe.

    "Who's there?" Olivia yelled out.

    "Hey! Hey, relax. Olivia, it's just me, Dean."

    "Dean! Fuck you scared the hell out of me, kid."

    "Sorry, I didn't even consider you might come down here. You alright?"

    "Sure. A few years off my life, some extra white hairs to cover. I'm good."

    Dean tried not to laugh. "I'm sorry, really."

    "No, I'm sorry. You're trying to help and I'm being snippy. I just...I don't like the dark. Which should make my all the more thankful you're here. Plus, I have no idea what the hell I'm doing."

    "Here." Dean handed Olivia his flashlight and knelt to pick-up her busted one, before looking inside the fuse box. "Doubt there's much I can do. I heard the transformer blow, so I think we're at the mercy of the power company."

    "Terrific," Olivia grumbled.

    Dean noticed the waver in the beam of the flashlight, and thus the tremble of Olivia's hand holding it. "You really _don't_ like the dark, do you? I'm amazed you even came down here."

    "Well, I'm not really afraid of basements, and figured if there was a chance to get the power back..." Olivia sighed. "Now though, I just kinda want to get back to my apartment and light every candle I have."

    Dean didn't even think before he was stepping forward and putting his hands on Olivia's shoulders. "Nothing I can do down here anyway, so how about I just get you back up to your apartment, huh? Stick around to make sure you have enough candles?"

    Olivia looked up at Dean, his face cast in shadows she could still make out his warm smile. She felt entirely pathetic, yet all she could manage to do was bite into her lower lip and nod her head.

    Taking the flashlight from Olivia's still shaking hands, Dean aligned himself directly behind the woman, not hesitating to keep his body flush with hers as they made their way through the dark basement, and back upstairs to her apartment.

 

    "You know, I'll be alright now. I'm sure you need to get back to your brother." Olivia lit another candle, Dean still trailing her around the apartment as she gathered and lit all of them she could find. He'd been so close against her all the way back to the apartment, she could actually feel him twitching beneath his jeans.

    "I can near promise you he's still fast asleep. Left a note just in case. But you probably want to get back to bed yourself, so if you're sure you're OK..."

    "Stay?" Olivia kept her back to Dean. There was far more than fear in her word, the desire she felt bleeding out into the request. If she didn't look at him though, if he turned her down, she could still manage to pretend it was nothing. And things wouldn't have to be awkward.

    Dean took a step forward, not quite closing the distance between them, not quite sure if he was reading her right. "Yeah."

    Olivia spun around, eyes focusing intently on Dean's face, searching for final confirmation to back up his breathy and heated reply, before her gaze swiftly trailed down his body. If his face wasn't indication enough, the straining bulge in his jeans was. "Fuck, kid." Olivia tentatively placed her hands on Dean's bared chest, shivers coursing through her body as her fingertips met soft, warm skin.

    " 'm not a kid." Dean closed the distance this time, taking Olivia firmly by the shoulders and pulling her to him.

    Ducking her head down, forehead resting against firm muscle, Olivia huffed out a strained laugh. "Young enough to be _my_ damn kid."

    Dean placed a finger under Olivia's chin, coaxing her to look up. "But I'm not." Bending down, Dean's lips ghosted over Olivia's. He drew back, hungry gaze dancing over her face, before going back in to flick his tongue over her lower lip; pulling back once more, then finally diving in to claim her mouth hard and dirty.

    Tiny, broken moans and whimpers poured from Olivia, as she opened up to Dean's _maybe not so much a kid_ assaulting kisses. He was all self-assured confidence, tongue thrusting into her mouth without hesitation. And the things he was doing with that tongue, made Olivia momentarily question who was really the older and more experienced of the two. Pulling back from the kiss, Olivia wobbled slightly as she held off Dean chasing her lips. She needed a breath. "I...uhh...p...point taken." Olivia took another deep breath, knowing full well it may be the last one she got for awhile. Handing Dean a nearby candle, and taking one herself, she took his free hand in hers and began to guide him gently. "Bedroom."

    Dean nodded, willingly letting her lead him.

    Setting the candle down on the dresser, Olivia turned around and grinned at Dean, slowly walking backwards towards the bed as she drank him in. "Clothes...off."

    Dean was more than willing to get on board with that, especially since Olivia was leading the way - her robe already on the floor, and nightshirt being pulled over her head. Dean flung off his shirt, toeing off his shoes and fumbling with the button on his jeans, as he got his first glimpse of Olivia's bare breasts. He'd expected impressive, but this...they...Dean raced forward, abandoning his efforts to fully work off his jeans, only to be halted by Olivia's waggling finger.

    "Off, Dean." Olivia pointed to his undone pants, smirking as she moved her hands to roll and pinch her nipples.

    "SonOfABitch," Dean mumbled, gaze fixed on Olivia's taunting fingers as he hopped on one leg, then the next, to rid himself of the offending denim.

    "Those too." Olivia indicated his boxers, before pulling at the elastic of her bikinis and slowly wiggling out of them.

    Dean started to move forward, then stopped, a very unmanly whine he would never admit to welling up out of him. "Now?" he pleaded.

    Olivia chuckled, "Ahh youth," and nodded her permission to a near frantic Dean.

    Lunging forward, Dean wrapped his arms around Olivia’s waist, sweeping her off the floor and carrying them both sideways to land on the bed. Olivia laughing and pinned under him, Dean kissed her hard; eager hand reaching down to finally palm and caress one perfect breast.

    Arching up into the worshiping touch, Olivia let her fingers twine in Dean's hair, pulling him deeper into their kiss - desperate to give back as good as the kid gave. On the next swipe of his tongue, Olivia caught his tongue gently between her teeth, slowly beginning to suck on the slick muscle, electing both a low moan and a harsh thrust of Dean's hips.

    Dean laid there panting and dizzy, Olivia's maneuver sending a too quick rush of blood straight to his dick. "Tell me what you want, Olivia? Want to make you feel good."

    Olivia cupped Dean's face in her hands. Pulling him down, she peppered him with kisses: brow, eyes, freckled nose and cheeks, over his stubbly jaw, and ever so softly on his lips. Most grown men (at least the ones she'd met) weren't this openly concerned about her pleasure, she certainly wasn't expecting it from an over-eager teenager with one hell of a raging hard on. "Your mouth, Dean, on me, over me, teeth biting, lips sucking...tongue inside me. Work me over, then fuck me hard."

    "Hell yeah," Dean groaned, pressing down to kiss Olivia forceful and deep, then moving to bite none-to-tenderly into the soft flesh of her throat. She gasped and tilted her head back, Dean licking the wound and sucking with gentle pressure as she wiggled underneath him. Satisfied with the red and purple mark, Dean trailed down to lap at the hollow of her throat; fingers pinching and twirling a nipple before he slid down to take it into his mouth. Centering his body over hers, Dean easily cupped Olivia's breasts, pushing the gloriously heavy mounds together to take turns mouthing alternately between them.

    Olivia panted, breathless. Blood rushing through her like hot lava as she watched Dean, his mouth opening impossibly wide to latch on over each breast. She didn't know if the kid was just a natural, or had seriously gotten around for his young years, but the things he was doing made her toes curl - literally. Perfect just-this-side-of-painful suction; teeth scraping and biting her nipples, crossing the threshold of pain; rippled and slick underside of his tongue soothing over the hardened nubs. Just when she thought she couldn't take anymore, Dean released his hold on her, pushed up off of her body, and dropped his head to lick a stripe down her chest, dipping into her bellybutton, then straight down into her neatly trimmed patch of hair.

    Laying flat on his belly between Olivia's thighs, Dean gently pushed her legs wider, ducking his head down to nuzzle his nose along her closed slit. Tongue darting out, he used the tip to slowly dip in and coax open her lips, pushing in further when he caught the first taste of her arousal, heady and intoxicating, against his tongue. Chasing the flavor, Dean twirled his tongue all around her entrance as Olivia moaned; hips grinding hard against Dean until he thrust into her, fucking her as deep as possible with his tongue, sending her arching up off the bed. One hand on her belly, easing her back down, Dean pulled back, using his other hand to spread her open allowing access to her clit.

    "Dean! Dean! Fuck...yes!" Olivia cried out, fingers clutching desperately both at the bedspread and Dean's hair. Dean's lips covered her clit, tongue teasing over the highly sensitive bud as he sucked. Her head swam with pleasure, nearly all of her focus on that tiny part of her body, and the oh-so-fucking-good pressure mounting between her thighs. Despite the overwhelming intensity, some part of her was still vaguely aware of Dean's finger. Ever so slowly he trailed it down her slit, dipping into her cunt, only to pull out and continue a little further down before stopping...hesitating.

    "Can I?" Dean let off of Olivia's clit, just long enough to ask permission for what he was certain she knew he wanted to do.

    "Fuckin' hell, kid! You're gonna kill...unhh...yes! Do it." Olivia threw her head back against the bed, resigned to Dean being some sort of Greek god of sex stuck in the body of a teenage boy.

    Dean smirked, and let out a low growl as he teased his finger down to where slick had pooled against Olivia's tight pucker. Petting softly against the furled flesh, coaxing the muscle to give, Dean eased in to the first knuckle, wiggling the tip of his finger in the tight heat. Pulling back out, he coated his finger in Olivia's arousal, then simultaneously sucked harder on her clit as he thrust his finger all the way up into her clenching hole.

    Olivia felt like an explosion had gone off. Wave after wave of tingling heat coursing through every inch of her, as she cried out Dean's name over and over.

    Crawling up her trembling form, Dean looked down at Olivia, soothing a hand over her flushed face. It was obvious she was fully caught in the clutches of her orgasm, yet not even waiting for her to come down, Dean gripped her thighs, pulled them up either side of his chest, and with one smooth, hard rock of his hips, slammed up into her spasming body.

    "Dean! Dean...oh fuuuuuck!" Still entirely alight with the sensations of her release, Olivia shockingly felt the next one ready to piggy-back it; Dean's body pistoning into her with short, hard thrusts, her inner walls aching with a desperate searing tension. One extra deep jab of his cock, and she was digging her nails into his back as the scream caught in her throat.

    Head thrown back, spine arched, Dean pounded into Olivia's body three...four more times before he grunted out his release; the continuing clenching inside Olivia milking him of every last drop.  
    The both of them sweaty, panting, spent, yet satisfied, Dean collapsed on the bed next to Olivia. "That was...are you..."

    "Mmm," Olivia moaned, lazy and content. " 'm fine, as long as I don't have to think, or move, or breathe."

    "Was that...was I...alright?"

    Olivia laughed, rolling onto her side and petting down Dean's chest. "Alright? You just gave me multiples, and ask if it was alright? Damn, kid."

    "Yeah, well, I aim to please, but I just wanted to...ya know...make sure."

    "Oh, honey, I'm sure and then some. Next time though, think I'll be the one to curl _your_ toes, and make you cum so hard you forget your own name."

    "Next time?" Dean questioned, voice hushed and uncertain.

    Olivia pulled her hand away from Dean's sweat slick chest, wishing desperately she had chosen her words more carefully. "I...I'm sorry. I shouldn't have... It's not a big deal, this was great. Just the once."

    Dean turned on his side. Worrying at his lower lip, he stared at Olivia before sighing deeply. "My dad could turn up tomorrow, and I could barely have time to drop off the keys before he's got Sammy and me packed and on the road. But if given the chance, I'd like a next time."

    "You don't...we don't..."

    "No, I want to. You just have to know..."

    "Right." Olivia nodded, and placed her hand back against Dean's chest, teasing a nipple with her fingernail. It wasn't like she had expected some happily-ever-after with the kid, just wanted some damn fine sex while she had the chance. Really, what he was offering was perfect. "So, we just...have a little fun. While we can."

    Letting out a low hiss, his body arching into the playful pinch of Olivia's fingers, Dean licked his lips, slow and deliberate. "Yeah. I can get on board with that."

    "Good." Olivia tilted up to catch Dean's lips, pressing a hard kiss against him. "Now, get the hell out of my bed and go home. You've got a kid brother who might wake-up worried, plus you have work early tomorrow. I'm sure I'm gonna have lots of cranky tenants if the power doesn't come back by morning."

    Dean groaned, giving Olivia one last kiss before rolling out of her bed, then gathering and pulling on clothes in the dark. "You know, I'm deeply wounded you aren't begging me to stay."

    Olivia shook her head, eyes focused on Dean's sultry pout, before grabbing a pillow and chucking it at him. "You can let yourself out...kid."

 

**x~X~x**

  
    Dean quietly let himself back into the apartment, hoping Sam was still asleep. Creeping down the hall, heading to look in on his brother, Dean nearly jumped out of his skin as the bathroom door opened. Sam stood there, hair sleep tousled, rubbing his eyes. "Shit, Sammy, you scared the hell out of me."

    "Sorry." Sam yawned. "Why you dressed? And why aren't the lights working? 's dark."

    Dean quickly realized Sam hadn't even known he was gone. "Don't worry 'bout it. Storm just knocked out the power and I went to check on things. Go back to sleep."

    " 'k." Sam yawned again, voice muzzy and sleep soft as he moved to slide past Dean, pausing as he inhaled deeply at the end of his yawn. "Dean?"

    "Yeah?"

    "Dude, you smell like sex."

    "What?" Dean squeaked. "I don't...I didn't...how the hell would you know what sex smells like!"

    " 'cus you're my brother. Shared enough rooms with you after a _conquest_."

    Dean rubbed at the back of his neck. "Sam, just go to bed."

    "I don't get it, she's old enough to be our mother!"

    "Promise you Sam, when you're older, you'll learn to appreciate the benefits of an older woman. Plus, she's freakin' hot."

    "Whatever, man." Sam yawned once more, air catching in his throat as Dean cuffed him on the back of the head. "Jerk!"

    "Go to bed, bitch."

 

 

x~X~x  _Benefits_   x~X~x

 

 

 


End file.
